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Merck

T3634

(+)-α-Tocopherol

from vegetable oil, Type V, ~1000 IU/g

Sinónimos:

2,5,7,8-Tetramethyl-2-(4′,8′,12′-trimethyltridecyl)-6-chromanol, 5,7,8-Trimethyltocol, D-α-Tocopherol, Vitamin E

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Acerca de este artículo

Fórmula empírica (notación de Hill):
C29H50O2
Número CAS:
Peso molecular:
430.71
NACRES:
NA.79
PubChem Substance ID:
eCl@ss:
34058016
UNSPSC Code:
12352205
EC Number:
200-412-2
MDL number:
Beilstein/REAXYS Number:
4712525
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biological source

vegetable oil

Quality Level

type

Type V

form

viscous liquid

specific activity

~1000 IU/g

color

clear yellow to red

refractive index

n20/D 1.505 (lit.)

bp

200-220 °C/0.1 mmHg (lit.)

density

0.95 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCc2c(C)c(O)c(C)c(C)c2O1

InChI

1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3/t21-,22-,29-/m1/s1

InChI key

GVJHHUAWPYXKBD-IEOSBIPESA-N

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General description

This product is miscible with chloroform or ethanol. It is practically insoluble in water but it is miscible with ether, acetone, and vegetable oils. It is unstable to alkaline conditions.
α-Tocopherol is synthesized from γ-tocopherol by the action of enzyme γ-tocopherol methyltransferase. It is the major form of Vitamin E in human plasma. It is present in sunflower seed oil.

Application

(+)-α-Tocopherol has been used:
  • as a food supplement for juvenile cobia fish
  • to evaluate its protective effect on bisphenol A induced oxidative stress in rats
  • to test its chemopreventive efficacy in estrogen-mediated mammary cancer rats

Biochem/physiol Actions

Tocopherols (TCP) (vitamin E) are a series (α, β, γ and δ) of chiral organic molecules that vary in their degree of methylation of the phenol moiety of the chromanol ring. Tocopherols are lipid soluble anti-oxidants that protect cell membranes from oxidative damage. α-Tocopherol is the form of tocopherol preferentially absorbed by homo sapiens. Various isofroms and analogues of tocopherol have opposing and differentiated regulatory activities in vivo.
α-Tocopherol is essential for the photosynthesis in Synechocystis sp. strain PCC 6803. Supplementation with α-Tocopherol decreases lipid peroxidation and platelet aggregation. It inhibits protein kinase C and may play key role in gene regulation.

Packaging

Packaged under argon in a sealed ampule.

Analysis Note

Approx. 670 mg D-α-tocopherol per gram. The non-α content is typically between 5-35 mg/g

Other Notes

Mixed constitutional (α, β, γ, δ) isomers.

Disclaimer

Subject to air oxidation.

Clase de almacenamiento

10 - Combustible liquids

wgk

WGK 1

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)


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Visite la Librería de documentos

alpha-Tocopherol is essential for acquired chill-light tolerance in the cyanobacterium Synechocystis sp. strain PCC 6803
Yang Y, et al.
Journal of Bacteriology, 190(5), 1554-1560 (2008)
Dietary alanyl-glutamine and vitamin E supplements could considerably promote the expression of GPx and PPARalpha genes, antioxidation, feed utilization, growth, and improve composition of juvenile cobia
Ding Z, et al.
Aquaculture (Amsterdam, Netherlands), 470(6), 95-102 (2017)
The role of alpha-tocopherol in preventing disease: from epidemiology to molecular events
Azzi A, et al.
Molecular Aspects of Medicine, 24(6), 325-336 (2003)
Blood alpha-tocopherol, gamma-tocopherol levels and risk of prostate cancer: a meta-analysis of prospective studies
Cui R, et al.
Testing, 9(3), e93044-e93044 (2014)
Differential gene regulation and tumor-inhibitory activities of alpha-, delta-, and gamma-tocopherols in estrogen-mediated mammary carcinogenesis
Gupta S, et al.
Cancer Prevention Research (Philadelphia, Pa.), 10(12), 694-703 (2017)

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